US5595727A - Aqueous cosmetic composition for setting the hair based on the combination of hydrodispersible polycondensate and a hydrosoluble copolymer - Google Patents

Aqueous cosmetic composition for setting the hair based on the combination of hydrodispersible polycondensate and a hydrosoluble copolymer Download PDF

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Publication number
US5595727A
US5595727A US08/447,171 US44717195A US5595727A US 5595727 A US5595727 A US 5595727A US 44717195 A US44717195 A US 44717195A US 5595727 A US5595727 A US 5595727A
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United States
Prior art keywords
cosmetic composition
hydrodispersible
percent
polycondensate
composition
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Expired - Fee Related
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US08/447,171
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English (en)
Inventor
Jean-Michel Sturla
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LOreal SA
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LOreal SA
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Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/02Cosmetics or similar toiletry preparations characterised by special physical form
    • A61K8/04Dispersions; Emulsions
    • A61K8/046Aerosols; Foams
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/81Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
    • A61K8/8141Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • A61K8/8147Homopolymers or copolymers of acids; Metal or ammonium salts thereof, e.g. crotonic acid, (meth)acrylic acid; Compositions of derivatives of such polymers
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/85Polyesters
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/06Preparations for styling the hair, e.g. by temporary shaping or colouring
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00Drug, bio-affecting and body treating compositions
    • Y10S424/01Aerosol hair preparation
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S424/00Drug, bio-affecting and body treating compositions
    • Y10S424/02Resin hair settings

Definitions

  • the present invention has for an object a cosmetic composition for setting hair containing in an aqueous or weakly hydroalcoholic medium, a combination of a hydrodispersible polycondensate having sulfonate functions and a hydrosoluble copolymer constituted by at least units having a neutralized carboxylic acid function and by units having a cyclic ester function.
  • compositions having strong alcohol content comprise a mixture of at least one hydrodispersible resin consisting of a polycondensate having sulfonate functions and a hydrosoluble resin consisting between others in a vinyl acetate/crotonic acid or vinyl acetate/crotonic acid/vinyl neodecanoate copolymer.
  • the present invention has then for an object an aqueous cosmetic composition for setting the hair containing in an aqueous or slightly hydroalcoholic medium:
  • R, R' and R" each independently, represent hydrogen or methyl
  • n and t are 1 or 2
  • R 1 represents linear or branched, saturated or unsaturated alkyl having 2 to 21 carbon atoms
  • Z represents a divalent radical selected from the group consisting of --CH 2 --, --CH 2 --O--CH 2 and --CH 2 O--(CH 2 ) 2 -- and
  • Cyc represents a member selected from the group consisting ##STR2## wherein
  • R 2 represents hydrogen or methyl
  • R 3 represents hydrogen, methyl, ethyl, tert-butyl, ethoxy, butoxy or dodecyloxy and
  • R 4 represents hydrogen, alkyl having 1-4 carbon atoms or alkoxy having 1-4 carbon atoms, and ##STR4##
  • v 10 to 90 percent and preferably 36 to 84 weight percent
  • w represents 3 to 20 percent and preferably 6 to 12 weight percent
  • x represents 4 to 60 percent and preferably 6 to 40 weight percent
  • y represents 0 to 40 percent and preferably 4 to 30 weight percent
  • the said carboxylic acid functions of said copolymer being neutralized by a basic agent in an amount greater than 80 percent.
  • the amount of the hydrodispersible polycondensate having sulfonate functions is between 2 and 30 weight percent relative to the total weight of the composition and that the hydrosoluble copolymer, such as previously defined, is preferably between 1 and 10 weight percent relative to the total weight of the composition.
  • the weight amount between the hydrosoluble copolymer and the hydrodispersible polycondensate is between 0.15 and 0.6.
  • this amount ranges from 0.2 to 0.4.
  • the hydrodispersible polycondensates having sulfonate functions employed in accordance with the present invention, generally have a vitreous transition temperature between 10° C. and 100° C. and preferably between 25° C. and 60° C.
  • Hydrodispersible polycondensates having sulfonic functions principally include, according to the present invention, copolyesters or copolesteramides.
  • the copolyesters are obtained by polycondensation of at least a dicarboxylic acid or one of its esters, at least a diol and at least a difunctional sulfoaryldicarboxylic compound substituted on the aromatic ring by a group --SO 3 M wherein M represents hydrogen or a metallic ion such as Na + , Li + or K + .
  • the copolyesteramides are obtained in the same manner as the copolyesters, but the polycondensation also makes equally intervening a diamine and/or an amino alcohol.
  • hydrodispersible polycondensates such as previously defined, are known and have been described principally in U.S. Pat. No. 3,779,993; U.S. Pat. No. 4,300,580 and EPO 0.540.374.
  • They generally have an average molecular weight between about 1,000 and 60,000 and preferably about 14,000.
  • hydrodispersible copolyesters and copolyesteramides having sulfonate functions exhibit the common characteristic of including at least units derived from isophthalic acid, dicarboxylic acid salt and diethylene glycol.
  • the hydrodispersible polycondensates having sulfonate functions are copolyesters having units derived from isophthalic acid, the sodium salt of sulfoisophthalic acid, diethylene glycol and 1-4 cyclohexanedimethanol. These units, respectively, are preferred and are present in amounts of 89/11/78/22 or 82/18/54/46.
  • copolyesters are commercialized under the names of AQ38® and AQ55® by Eastman Kodak.
  • the hydrodispersible copolyesters employed can additionally contain patterns derived from ethylene glycol, tri-and tetraethylene glycol and terephthalate.
  • the hydrosoluble copolymer responding to formula (I) preferably has an average molecular weight between 5,000 and 10 6 .
  • copolymers are not employed as such in compositions, according to the present invention, but must be previously neutralized to an amount greater than about 80 percent.
  • the hydrosoluble copolymers employed in accordance with the present invention are 100 percent neutralized.
  • the neutralization of the carboxylic acid functions is carried out using a basic agent selected for example from a mineral base such as soda or potash or an organic base selected from the group consisting of 2-amino-2-methyl-1-propanol (AMP), triethanolamine, triisopropanolamine (TIPA), monoethanolamine, diethanolamine, tri[(2-hydroxy) 1-propyl]amine, 2-amino-2-methyl-1,3-propanediol (AMPD) and 2-amino-2-hydroxymethyl-1,3-propanediol.
  • a basic agent selected for example from a mineral base such as soda or potash or an organic base selected from the group consisting of 2-amino-2-methyl-1-propanol (AMP), triethanolamine, triisopropanolamine (TIPA), monoethanolamine, diethanolamine, tri[(2-hydroxy) 1-propyl]amine, 2-amino-2-methyl-1,3-propanediol (AMPD) and 2-amino-2-hydroxymethyl
  • the amount of water is generally between 15 and 96.5% weight percent relative to the total weight of the composition.
  • the alcohol amount is generally less than 30 weight percent relative to the total weight of the composition and preferably between 1 and 15 percent.
  • useable alcohols preferably employed are alcohols having 2 to 5 carbon atoms and are, particularly, ethanol, isopropanol, or butanol.
  • the cosmetic compositions for setting the hair according to the present invention are principally present in the form of an aerosol lacquer, a setting lotion by manual pulverization, a setting lotion or even a covering foam.
  • the cosmetic compositions for setting the hair can also contain a plasticizing agent in an amount between 0.01 and 16 percent by weight relative to the total weight of the composition.
  • plasticizing agents being able to be employed in accordance with the present invention the following are mentioned:
  • CARBITOLS of Union Carbide namely CARBITOL® or diethylene glycol ethylether; METHYL CARBITOL® or diethylene glycol methylether; BUTYL CARBITOL® or diethylene glycol butylether; or also HEXYL CARBITOL® or diethylene glycol hexylether;
  • CELLOSOLVES of Union Carbide namely CELLOSOLVE® or ethylene glycol ethylether; BUTYL CELLOSOLVE® or ethylene glycol butylether; and HEXYL CELLOSOLVE® or ethylene glycol hexylether;
  • propylene glycol derivatives and in particular propylene glycol phenylether; propylene glycol diacetate; dipropylene glycol butylether; tripropylene glycol butylether;
  • DOWANOLS® of Dow Chemical namely DOWANOL PM® or propylene glycol methylether; DOWANOL DPM® or dipropylene glycol methylether; and DOWANOL TPM® or tripropylene glycol methylether.
  • ricin oil oxyethylenated with 40 moles of ethylene oxide such as that sold by Rhone Poulenc under the name MULGOFEN EL-719®,
  • triethyl citrate sold by Pfizer under the name CITROFLEX-2®.
  • glycerol esters such as glycerol diacetate (diacetin) and glycerol triacetate (triacetine).
  • compositions according to the present invention such as solar filters; polymers having, preferably a molecular weight lower than or equal to 500,000 such as a reticulated homopolymer of methacryloyloxyethyltrimethyl ammonium chloride; and the reticulated copolymers of acrylamide and a monomer chosen among (i) neutralized 2-acid-2-acrylamide methyl sulfonic propane, (ii) ammonium acrylate and (iii) methacyloyloxyethyltrimethyl ammonium chloride; proteins; silicones; anti-foam agents; hydrating agents; humectants; perfumes; preservatives; colorants; antioxidants, etc.
  • solar filters polymers having, preferably a molecular weight lower than or equal to 500,000 such as a reticulated homopolymer of methacryloyloxyethyltrimethyl ammonium chloride
  • a setting spray is prepared in a service pump bottle:
  • the container once filled, is then equipped with a spray pump.
  • the lacquer is easily removed during shampooing and the hair possesses good shine.
  • a setting spray is prepared by producing the following mixture:
  • the resulting lotion is then conditioned in a rechargeable spray diffuser in compressed air.
  • An aerosol lacquer for the hair is prepared by conditioning in an appropriate aerosol container:
  • the valve of the hair setter is attached and the container is hermetically closed.
  • the lacquer applied onto the hair rapidly drys, possesses a good cosmetic touch and is easily removed during shampooing.
  • a hair setting spray having the following composition is prepared in a pump bottle:
  • the lacquer After spraying, the lacquer exhibited good holding and is easily removed during shampooing.
  • a control spray (Spray D) is also prepared and only contains water.
  • Sprays B and C differ from the present invention's Spray A by the nature of the employed hydrosoluble copolymer.
  • the spray pump delivering a dose of 190 ⁇ l per spray.
  • the sample is soaked in a shampooing solution, rinsed, then is wound at a humid state on a 20 mm diameter hair curler.
  • the sample is then dried under a hood, allowed to cool, unrolled and then vertically suspended.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Cosmetics (AREA)
US08/447,171 1994-05-19 1995-05-19 Aqueous cosmetic composition for setting the hair based on the combination of hydrodispersible polycondensate and a hydrosoluble copolymer Expired - Fee Related US5595727A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR9406119A FR2719995A1 (fr) 1994-05-19 1994-05-19 Composition cosmétique aqueuse pour la fixation de la chevelure à base de l'association d'un polycondensat hydrodispersible et d'un copolymère hydrosoluble.
FR94-06119 1994-05-19

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6656458B1 (en) 1998-03-31 2003-12-02 L'ORéAL S.A. Poly-aminoacid derivatives and their use in compositions for treating keratinous fibres
US20060024259A1 (en) * 2004-07-29 2006-02-02 Sabine Vrignaud Cosmetic composition comprising, in a non-fatty medium, at least one linear sulfonic polyester and at least one nonionic thickening polymer, processes using this composition and uses thereof
US20060024261A1 (en) * 2004-07-29 2006-02-02 Bebot Cecile Cosmetic compositions comprising a linear sulfonic polyester and a polyurethane, processes using these compositions and uses thereof
US20060024260A1 (en) * 2004-07-29 2006-02-02 Cecile Bebot Cosmetic composition comprising a water-dispersible linear sulphonic polyester and a modified guar gum, methods employing this composition and uses
US20060188461A1 (en) * 2004-07-29 2006-08-24 Cecile Bebot Linear sulfonic polyester as a water-resistant hair fixing agent
US20100160454A1 (en) * 2008-12-22 2010-06-24 Eastman Chemical Company Antimicrobial agents, compositions and products containing the same, and methods of using the compositions and products
US20110028590A1 (en) * 2009-05-15 2011-02-03 Eastman Chemical Company Antimicrobial effect of cycloaliphatic diol antimicrobial agents in coating compositions
US20140079645A1 (en) * 2010-12-14 2014-03-20 L'oreal Aerosol device having two compartments including an alcoholic or hydroalcoholic hairstyling composition, and hairstyling method
US9867766B2 (en) 2015-12-17 2018-01-16 Sidiram S. Ragoonath Method of using a hair growth product

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6136884A (en) 1997-02-04 2000-10-24 Eastman Chemical Company Hair care compositions
US6749836B1 (en) 1998-01-30 2004-06-15 Eastman Chemical Company Hair care compositions
US6638992B1 (en) 1998-01-30 2003-10-28 Eastman Chemical Company Hair care compositions
FR2922449B1 (fr) * 2007-10-23 2010-01-01 Oreal Composition cosmetique comprenant au moins un polymere fixant anionique et la cyclohexylamine

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2439798A1 (fr) * 1978-10-27 1980-05-23 Oreal Nouveaux copolymeres utilisables en cosmetique, notamment dans des laques et lotions de mises en plis
US5158762A (en) * 1992-03-09 1992-10-27 Isp Investments Inc. Water-based hair spray compositions containing multiple polymers
WO1993011736A1 (fr) * 1991-12-13 1993-06-24 L'oreal Systeme aerosol pour laque capillaire
US5266303A (en) * 1992-11-30 1993-11-30 Eastman Kodak Company Aerosol hair spray formulations

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2439798A1 (fr) * 1978-10-27 1980-05-23 Oreal Nouveaux copolymeres utilisables en cosmetique, notamment dans des laques et lotions de mises en plis
US4282203A (en) * 1978-10-27 1981-08-04 L'oreal Hair lacquer and hair lotion compositions containing a copolymer having units of a vinyl allyl or methally ester of an α- or β-cyclic carboxylic acid
WO1993011736A1 (fr) * 1991-12-13 1993-06-24 L'oreal Systeme aerosol pour laque capillaire
US5158762A (en) * 1992-03-09 1992-10-27 Isp Investments Inc. Water-based hair spray compositions containing multiple polymers
US5266303A (en) * 1992-11-30 1993-11-30 Eastman Kodak Company Aerosol hair spray formulations

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7316815B2 (en) 1998-03-31 2008-01-08 L'oreal S.A. Polyamino acid derivatives and use thereof in compositions for treating keratin fibers
US7759378B2 (en) 1998-03-31 2010-07-20 L'oreal S.A. Polyamino acid derivatives and use thereof in compositions for treating keratin fibers
US20100092405A1 (en) * 1998-03-31 2010-04-15 L'oreal S.A. Polyamino acid derivatives and use thereof in compositions for treating keratin fibers
US6656458B1 (en) 1998-03-31 2003-12-02 L'ORéAL S.A. Poly-aminoacid derivatives and their use in compositions for treating keratinous fibres
US20060024260A1 (en) * 2004-07-29 2006-02-02 Cecile Bebot Cosmetic composition comprising a water-dispersible linear sulphonic polyester and a modified guar gum, methods employing this composition and uses
US20060188461A1 (en) * 2004-07-29 2006-08-24 Cecile Bebot Linear sulfonic polyester as a water-resistant hair fixing agent
US20060024261A1 (en) * 2004-07-29 2006-02-02 Bebot Cecile Cosmetic compositions comprising a linear sulfonic polyester and a polyurethane, processes using these compositions and uses thereof
US20060024259A1 (en) * 2004-07-29 2006-02-02 Sabine Vrignaud Cosmetic composition comprising, in a non-fatty medium, at least one linear sulfonic polyester and at least one nonionic thickening polymer, processes using this composition and uses thereof
US20100160454A1 (en) * 2008-12-22 2010-06-24 Eastman Chemical Company Antimicrobial agents, compositions and products containing the same, and methods of using the compositions and products
US20110028590A1 (en) * 2009-05-15 2011-02-03 Eastman Chemical Company Antimicrobial effect of cycloaliphatic diol antimicrobial agents in coating compositions
US8106111B2 (en) 2009-05-15 2012-01-31 Eastman Chemical Company Antimicrobial effect of cycloaliphatic diol antimicrobial agents in coating compositions
US20140079645A1 (en) * 2010-12-14 2014-03-20 L'oreal Aerosol device having two compartments including an alcoholic or hydroalcoholic hairstyling composition, and hairstyling method
US10758025B2 (en) * 2010-12-14 2020-09-01 L'oreal Aerosol device having two compartments including an alcoholic or hydroalcoholic hairstyling composition, and hairstyling method
US9867766B2 (en) 2015-12-17 2018-01-16 Sidiram S. Ragoonath Method of using a hair growth product
US10201486B2 (en) 2015-12-17 2019-02-12 Sidiram S. Ragoonath Method of making a hair growth product

Also Published As

Publication number Publication date
FR2719995B1 (el) 1997-02-07
FR2719995A1 (fr) 1995-11-24

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